Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C327/00—Thiocarboxylic acids
  • C07C327/20—Esters of monothiocarboxylic acids
  • C07C327/28—Esters of monothiocarboxylic acids having sulfur atoms of esterified thiocarboxyl groups bound to carbon atoms of hydrocarbon radicals substituted by singly-bound oxygen atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/62—Oxygen or sulfur atoms
  • C07D213/63—One oxygen atom
  • C07D213/64—One oxygen atom attached in position 2 or 6
  • C07D213/643—2-Phenoxypyridines; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
  • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
  • A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
  • A01N39/04—Aryloxy-acetic acids; Derivatives thereof
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C327/00—Thiocarboxylic acids

Definitions

• the invention relates to new, substituted alkane thiocarboxylic acid derivatives, a process for their preparation and their use as herbicides.
• Those substituted alkanethiocarboxylic acid derivatives of the formula (I) in which R 1 is methyl contain an asymmetric carbon atom in the side chain and can therefore exist in two enantiomeric forms.
• the invention relates both to the respective racemates and to the R and S enantiomers.
• the substituted alkane thiocarboxylic acid derivatives of the formula (I) according to the invention have better herbicidal properties than the 4- [4- (2,4-dichlorophenoxy) phenoxy] propionic acid methyl ester known from the prior art, which is a highly effective and constitutionally similar active ingredient Mode of action is.
• the active compounds of the formula (1) according to the invention some grass weeds which occur particularly in rice and are not affected by the methyl 4- [4- (2,4-dichlorophenoxy) phenoxy] propionate can be effectively combated .
• a preferred group of compounds according to the invention are those substances of the formula (I) in which A represents a CH group, X I represents trifluoromethyl, X 2 and X 3 represent hydrogen or chlorine, R 1 represents methyl and R 2 represents methyl or ethyl.
• Another group of preferred compounds according to the invention are those substances of the formula (I) in which -A is nitrogen, X 1 is chlorine or trifluoromethyl, X 2 is hydrogen or chlorine, X 3 is hydrogen, R 1 is methyl stands and R 2 stands for methyl or ethyl.
• Formula (11) clearly defines the phenoxyalkane carboxylic acid derivatives required as starting materials when carrying out the process according to the invention.
• A, X 1 , X 2 , X 3 , R 1 and R 2 preferably have those meanings which have already been mentioned for these radicals in connection with the description of the substances of the formula (I) according to the invention.
• phenoxyalkane carboxylic acid derivatives of the formula (11) are those substances which correspond to the alkane thiocarboxylic acid derivatives of the formula (I) listed in Tables 1 to 7.
• the phenoxyalkane carboxylic acid derivatives of the formula (11) are known or can be prepared in a simple manner by known methods (cf. DE-OS 32 19 789, DE-OS 32 21 214, DE-OS 32 19 821, BE-PS 862 325 , BE-PS 868 875, EP-OS 483, EP-OS 17 767, EP-OS 1 473, US-PS 4 301 295 and DE-OS 29 46 652).
• optically active phenoxyalkanecarboxylic acid derivatives of the formula (Ila) are also known or can be prepared by known methods (cf. literature cited above).
• the asymmetrically substituted carbon atom is identified by an ( * ).
• diluents Practically all inert organic solvents can be used as diluents. These preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin, benzene, toluene, xylene, chlorobenzene and o-dichlorobenzene, ethers, such as dibutyl ether, glycol dimethyl ether and diglycol dimethyl ether and tetrahanrofuran .
• diluents Practically all inert organic solvents can be used as diluents.
• diluents preferably include aliphatic and aromatic, optionally halogenated hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, gasoline, ligroin,
• reaction temperatures can be varied within a substantial range in the process according to the invention. In general, temperatures between 20 ° C and 190 ° C, preferably between 110 ° and 160 ° C.
• the process according to the invention is generally carried out under normal pressure. However, it is also possible to work under increased or reduced pressure.
• the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the two components in a larger excess.
• the reaction is generally carried out in a suitable diluent and the reaction mixture is stirred for several hours at the required temperature. This method is worked up using conventional methods.
• the procedure is expediently that the phenoxyalkanecarboxylic acid derivatives of the formula (Ila) in each case are first prepared by the method described in DE-OS 27 58 002 and these substances of the formula (Ila) are then converted into the corresponding thio compounds by the process according to the invention.
• the active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow up in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the compounds are suitable for total weed control, e.g. on industrial and track systems and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops e.g. Forestry, ornamental trees, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annual crops.
• the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• extenders that is to say liquid solvents and / or solid carriers
• surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
• organic solvents can also be used as auxiliary solvents.
• auxiliary solvents e.g. organic solvents
• aromatics such as xylene, toluene, or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chlorethylenes or methylene chloride
• aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• alcohols such as butanol or glycol and their ethers and esters
• ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• Adhesives such as carboxymethyl cellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
• the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used for weed control in a mixture with known herbicides, finished formulations or tank mixes being possible.
• Known herbicides such as e.g. 1-amino-6-ethylthio-3- (2,2-dimethylpropyl) -1,3,5-triazine-2,4 (1H, 3H) -dione or N- (2-benzothiazolyl) -N, N '-di-methyl-urea for weed control in cereals; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5 (4H) -one for weed control in sugar beets and 4-amino-6- (1,1-dimethylethyl) -3-methylthio -1,2,4-triazin-5 (4H) -one for weed control in soybeans, in question. Surprisingly, some mixtures also show a synergistic effect.
• a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
• the active compounds according to the invention can be applied both before and after emergence of the plants.
• the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates between 0.001 and 10 kg of active ingredient per hectare of soil, preferably between 0.01 and 5 kg per ha.
• Test plants which have a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area.
• the concentration of the spray liquor is chosen so that the desired amounts of active compound are applied in 2000 l of water / ha.
• the degree of damage to the plants is rated in% damage compared to the development of the untreated control.
• the active compounds (1), (4) and (5) according to the invention show a better selective herbicidal activity than the comparison substance (A.) In the control of alopecurus, echinochloa and setaria in sugar beets at a rate of 0.5 kg of active compound per hectare ).

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• Life Sciences & Earth Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Wood Science & Technology (AREA)
• Environmental Sciences (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Zoology (AREA)
• Pest Control & Pesticides (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Pyridine Compounds (AREA)
• Polysaccharides And Polysaccharide Derivatives (AREA)
• Detergent Compositions (AREA)
• Separation Using Semi-Permeable Membranes (AREA)
• Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

Priority Applications (1)

Applications Claiming Priority (2)

Publications (2)

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ID=6190279

Family Applications (1)

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• 1983
  • 1983-02-08 DE DE19833304204 patent/DE3304204A1/de not_active Withdrawn
• 1984
  • 1984-01-26 EP EP84100796A patent/EP0115823B1/de not_active Expired
  • 1984-01-26 AT AT84100796T patent/ATE27268T1/de not_active IP Right Cessation
  • 1984-01-26 DE DE8484100796T patent/DE3463765D1/de not_active Expired
  • 1984-02-06 IL IL70875A patent/IL70875A/xx not_active IP Right Cessation
  • 1984-02-06 CA CA000446839A patent/CA1192555A/en not_active Expired
  • 1984-02-06 TR TR21906A patent/TR21906A/xx unknown
  • 1984-02-06 JP JP59018500A patent/JPS59148758A/ja active Pending
  • 1984-02-06 GR GR73709A patent/GR81408B/el unknown
  • 1984-02-07 ES ES529521A patent/ES529521A0/es active Granted
  • 1984-02-07 BR BR8400535A patent/BR8400535A/pt unknown
  • 1984-02-07 ZA ZA84892A patent/ZA84892B/xx unknown
  • 1984-02-07 IE IE281/84A patent/IE56764B1/xx unknown
  • 1984-02-07 PH PH30209A patent/PH20475A/en unknown
  • 1984-02-07 DK DK54484A patent/DK54484A/da not_active Application Discontinuation
  • 1984-02-07 NZ NZ207059A patent/NZ207059A/en unknown
  • 1984-02-07 HU HU84501A patent/HU194023B/hu unknown
  • 1984-02-08 AU AU24282/84A patent/AU561124B2/en not_active Ceased
  • 1984-02-08 KR KR1019840000587A patent/KR850000390A/ko not_active Application Discontinuation
• 1985
  • 1985-05-22 US US06/736,748 patent/US4599106A/en not_active Expired - Fee Related

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